


A Date to remember

by NotfunnyDean (IronEyes)



Category: Supernatural
Genre: Dean doesn't even realize it's a date, First Date, M/M, Soft Benny, Sweet Dean, Valentine's Day, Valentine's Day Fluff, gentleman benny, the sweet idiot
Language: English
Status: Completed
Published: 2019-02-15
Updated: 2019-02-15
Packaged: 2019-10-29 05:00:02
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,616
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17801483
Author URL: https://archiveofourown.org/users/IronEyes/pseuds/NotfunnyDean
Summary: It's Thursday and Sam is busy preparing for a date. Dean has no idea, why he would go out on a freaking Thursday but that leaves Dean to do nothing, until Benny wants to meet him.





	A Date to remember

**Author's Note:**

  * For [smartravenclaws](https://archiveofourown.org/users/smartravenclaws/gifts).



> Hey this was a Valentine's Day surprise for my very own Benny :p

Dean wasn’t pouting. _He wasn’t!_

“Dean can you stop doing that?” Sam asks from his place behind the laptop. Dean sits at the opposite end of the table and frowns at his brother and his way too good mood.

“Stop doing - _what?_ ” Dean asks back and he plays with the empty beer bottle in his hand. He is freaking bored and it’s the middle of the week. They already finished their latest hunt and now Dean doesn’t know what to do with himself.

“Pouting.” Sam grins and he gets up. He goes over to his motel bed and reaches for his bag. Dean pushes his lower lip even further out. He wasn’t pouting. 

“Why can’t we just drive home?” Dean whines and he rolls his eyes, while Sam doesn’t even look at him, but instead gets one of his nicer dress shirts out of his bag. It’s dark blue and Dean squints. Since when does Sam have an actual taste in fashion.

“I told you. I met someone at the bar and we want to go out.” Sam explains and Dean nods. Yeah, Sam told him that before. It’s still weird. Normally Dean is the one who goes out with a woman, but lately…

Yeah, it doesn’t feel so good anymore.

“It’s Thursday, who wants to go out with you on a Thursday?” Dean complains and Sam just chuckles, before he goes over to the bathroom to change. 

“So, it’s Thursday. That never bothered you before.” Sam just grins and Dean nods. Yeah, it never really mattered to him, which day it was. He just wanted to get lucky. 

Dean walks over to his own bed and searches for his phone. He could ask Castiel if he had some spare time and would go out drinking with him. Then again, Dean already had enough beer...and heck did he just really think that?

“Oh.” Dean says when he looks at his phone.

“Everything alright?” Sam asks and looks out of the bathroom. His hair is still wet, but he is already dressed. Dean frowns at the clean shoes. Seems like Sammy really means it today.  
“Yeah just...Benny texted.” Dean admits. He isn’t sure what Sam thinks of Benny. At first he really hated the vampire, but things seem to have calmed down in the last weeks and Benny would even help them out sometimes.

“What does he want?” Sam says and Dean rolls his eyes, when Sam starts to brush his hair. That girl.

“Oh, just asked me if I’m free tonight.” Dean mutters. He turns a bit away from Sam, so his damn brother can’t see how Dean blushes at the thought. He...okay maybe he does have a crush on Benny. Sue him.

“Well, you are, right?” Sam says and puts his stuff away. He turns a few times in front of the mirror and Dean shrugs. Normally, Sam is always going with them. Maybe because Sam doesn’t trust Benny, but maybe also because Dean isn’t sure what he would do, when he is alone with the vampire. 

“Yeah but…” Dean tries and now of course his brother looks at him through the damn mirror. Urgh.

“Seriously, if he’s nearby, then why not meet him.” Sam says and this time he goes over to Dean’s bag. Privacy? They don’t really know that anymore. Dean looks back at his phone. Benny already told him yesterday, that he also has a case. Not even an hour away. 

Over the past few months Benny spend his days on hunting vampires. Dean is a bit impressed and also a bit aroused. He texts Benny the name of his motel and waits.

“Yeah…” Dean starts to say, just as Sam throws something right into his face. Dean sputters and then glares at his brother. 

“Wear that and maybe shower.” Sam says casually and Dean looks at the dress shirt in his hands. It’s deep red and it actually looks really good. Dean frowns. When the heck did he buy this?

“Why would i dress up like this.” Dean says and he hopes it’s not too obvious how much he would love to wear that for Benny. Sam just rolls his eyes and then starts to brush his hair again. 

Dean sighs. Maybe...he could actually enjoy a nice evening out with Benny. And if he dressed up like that...he could find someone to spend the night with. 

Right.

 

*

 

An hour later Sam is already gone and Dean spends his time walking around the tiny motel room. He is actually nervous and he doesn’t even know why. He looks in the mirror. 

He is wearing the tight red shirt and dark jeans. He even cleaned his damn boots and he feels a bit silly now. Benny just wants to drink a few beers. Nothing special. 

Just a guy’s night out.

Yeah.

“Dean?”

There is a knock on his door and Dean takes a deep breath, before he opens it. Benny leans in the doorway and is grinning widely. Even though they had seen each other a lot the last months, Dean smiles.

“Hi Benny.” He says and he chuckles a bit embarrassed, when Benny looks him up and down. It takes him a lot, not to squirm under his gaze.

“Cher.” Benny says in his deep voice and then he is already hugging Dean. He always liked it a lot, when Benny called him that. Dean hugs him back and tries not to get lost in the embrace.

While Dean knows that he is strong himself, he doesn’t look like it. Sam and Benny always look a bit stronger than him. But Dean really likes Benny’s arms. A lot. He shakes his head and takes a step back.

“You look good, Dean.” Benny says and Dean’s eyes widen at the compliment. He plays with the hem of his shirt and blushes. Dean hastily turns around and searches for his suit jacket.

“You ready?” Benny asks then and Dean nods. Only now does he take a real look at Benny and swallows dryly. Benny wears a nice suit. Holy crap.

“Y-yeah. Were you still working before you drove here?” Dean wants to know, because maybe Benny is doing some FBI work now, too. It would fit him. He does look stunning in the dark blue suit and Dean is sure most people would give him any information he asks for.

“Oh. Yeah, nothing big, though. I already handled it.” Benny says and he walks over to his car. Dean glances at Baby and then sighs. He could give her some rest for once. So he doesn’t even say anything and follows Benny to his old jeep.

“So, I found us a little restaurant in the next town.” Benny says and then he goes over to the passenger door. For a second Dean is confused. Doesn’t Benny want to drive? But then Benny actually holds the door open for him and Dean ducks his head, before he sits down on the leather seat. 

“Thanks.” Dean mutters and he can’t look Benny in the eye. Somehow this feels a bit weird. While Benny always calls him Cher or other nicknames, he never told Dean before that he looked good or held a door open for him.

“Heard they have the best burgers and also some delicious pie.” Benny says, when he sits down behind the steering wheel and Dean’s treacherous belly rumbles at the thought. Benny laughs. 

“A man after my own heart.” Dean says and his mouth feels way too dry. Why did he say that? But Benny doesn’t seem to be bothered by it. No, he even pats Dean’s thigh and then shifts his focus back on the road.

Dean’s heart makes a salto at that. Maybe he should check Benny’s car for some hexbags. 

“Here, I bought this for you.” Benny says and he is grinning, when he presses a few cassettes in Dean’s hands. They are really old ones and Dean hastily checks them. There are a lot of his favorite songs on them.

“Woah. You finally gained a better taste in music?” Dean asks and he and he puts on one of the Led Zeppelin tapes. Benny just chuckles and he even turns up the volume a bit. Dean sighs contentedly. This might be the start of a perfect evening.

“Let’s just say I know how to make you happy.” Benny says and Dean isn’t sure what he should answer to that. He doesn’t need his favorite music to be happy around Benny. The vampire alone is more than enough.

Dean looks out of the window. He kinda wishes Benny would put his hand on his thigh again. Instead, they spend the next minutes in silence. Dean doesn’t even hum to the music.

“Oh wow.” Dean only says, when Benny parks his car at the restaurant. This looks damn expensive and Dean is glad he took real money with him to pay. Not sure this restaurant would be happy with his fake credit card.

“Yeah, it does look good.” Benny agrees and gets out of the car. Dean puts the cassettes Benny gave him into the center console and wants to open his own door. Just to see that Benny is already standing there, opening it for him. Dean smiles.

He didn’t know Benny was such a gentleman, but it does fit him.

Inside the restaurant, Dean takes a look around. It really is a nice place and it’s almost completely full. How the heck would they find a table for them. At least he doesn’t look like a lumberjack in his dress shirt and dark jeans. 

“Two for Lafitte.” Benny says and Dean raises his eyebrows. Benny reserved them a table beforehand? Well that is kinda nice. Maybe Dean should make use of that more often, too. 

“One table in the back. If you would be so kind as to follow me, I’ll get you to your table,” the lady behind the counter says and Benny takes Dean’s hand as he follows her. 

_Oh god._

Dean feels as if everyone is looking at them. Does Benny think Dean is too stupid to follow them both? Or maybe he holds his hand, because the aisles between the tables here are really a bit cramped. 

“This is your table, I will be back with the menus,” the lady says again and points at their table. There are some candles on it and even a freaking flower. Dean looks around.

Well, okay. Every table looks like this. The whole restaurant has flowers and candles everywhere. And there are even some hearts on the windows. Dean shudders at bit. This looks like Cupid’s house. 

“I feel like a good cheeseburger.” Benny announces and Dean focuses back on him. He nods. Yeah, a burger sounds good. 

“I hope you are right and the burgers are as good as you think.” Dean says and he thanks the waitress, when she hands them the cards. Since they already know what they want, they each order a cheeseburger with fries and a cold beer. Dean rubs his hands. He is so hungry.

“I would never take you out to a place, that doesn’t have good burgers.” Benny says then and Dean wishes he had the menu back, so he could hide behind it. Benny really says some things today, that make Dean nervous. Happy, but also nervous. 

“T-thank you.” Dean says dumbly and Benny chuckles. Dean loves that sound. He loves everything about Benny’s voice and oh god...did he just think...loves?!

Then again it’s not that much of a surprise. Though Dean never acted on it, he always knew that men attract him just as much, as women do. Maybe...well he would actually burn his fears for Benny.

“So tell me Cher, how are you?” Benny asks and this time he actually puts his hand over Dean’s sweaty one. Dean actually gasps at their hands for a second, but then the waitress comes back and she winks at Dean.

_Oh._

Maybe Benny wanted her to think they are a couple, so she wouldn’t start flirting with Dean and destroy their...best friend evening. Or whatever something like this is called. 

Dean takes his plate and his belly rumbles again. Oh yes, this looks really good. Benny just laughs, when Dean already starts eating. He doesn’t even care about his manners. He just stuffs his face with the fries and groans.

So damn good.

“Slow down, it’s not going anywhere.” Benny says and he winks at Dean. This time he feels a lot more intimated and hopes Benny thinks his blush is caused by the heat in this room.

“But it’s so good!” Dean complains, but he does try to eat like a normal human being. Benny eats his burger slowly, but even he groans around a few mouthful and Dean wiggles a bit on his seat.

So not the time for something like this.

“Told you this is a very good place.” Benny smiles and Dean grins back at him. Only then he remembers, that his mouth is still full of fries and he hastily swallows. He is a bit embarrassed, but Benny doesn’t seem mad at him.

“We should come here more often.” Dean says and drinks a sip from his beer. The restaurant is roughly three hours away from the bunker, but Dean would drive a lot more hours for a burger like this. 

“I’d like that.” Benny whispers and then he smiles so warmly at Dean, that Dean has to look away. He is a bit overwhelmed by all of this. Damn feelings. He was better off without them.

Benny is still grinning at him, when Dean looks back.

“What?” Dean mumbles and okay that sounded way too shy for him. Benny just reaches for his napkin and then holds it towards Dean’s face.

“You got something there.” Benny says quietly and he carefully presses the napkin against the corner of Dean’s mouth. He is very gentle while he does it and Dean kinda wants to grab his hand, only to kiss it. 

“Oh. Thank you.” Dean says dumbly again and Benny smirks at him. Well that shouldn’t be as hot as it is. 

“Would you like any dessert?” The waitress asks, when they finished their burgers and Dean looks up at her. She is really pretty, he only realizes that now. He hadn’t really looked at her, because he was so focused on Benny.

He is so gone.

“Well, I think my cher would like some cherry pie, right Dean? Nothing for me, but maybe I’m lucky and he shares his pie with me.” Benny says easily and Dean gasps at him. The waitress chuckles again. 

“No problem.” She says and takes their empty plates with her. 

“She was a bit intrusive right?” Dean chuckles a bit helplessly. He hadn’t seen her flirting with him, but if Benny did something like that, he must’ve seen something. 

"You think so?" Benny asks back and he seems a bit confused at that. Dean shrugs and then waits patiently for his pie. When the waitress comes back, Dean can see how Benny checks her out now. Dean frowns.

He doesn't like it when Benny looks at other people.

The waitress puts the pie down in front of Dean, but she gives Benny a fork, too. Dean waits for her to go, before he looks back to Benny.

"Did you really want something?" Dean asks and Benny grins, before he actually takes the cherry on top of the pie and eats it. Dean gasps.

"Hey! That's the best part." Dean says and then he starts laughing, when Benny grins at him, before he takes the other cherry, that is placed on the pie.

"I know." Benny grins and then he even holds his fork up for him. Dean looks around, making sure that nobody is watching them and then hastily eats from the fork Benny holds up. He blushes badly again, but Benny's smile is worth it.

"It's really good." Dean stammers, when he looks back at his plate. This evening is so, so weird. But at the same time, Dean never wants it to stop.

They spend the next minutes eating the pie and laughing together. Dean manages to eat only a bit more than Benny, but it was nice to share the pie with him.

Dean isn't sure how many hours they are in that restaurant, but they end up ordering some freaking ice cream. Benny tells him more about the time before purgatory and Dean tells him about the time Sammy got drunk for the first time.

It's a lovely night and fun and Dean is almost disappointed, when Benny waves at their waitress to pay the bill. Dean fumbles for his money, but Benny shakes his head.

"Nope. I asked you out, remember, Cher?" Benny says and Dean nods. Asked him out? That's not really a term he would use. But he lets Benny pay for the food and the drinks and then follows him back outside to the car.

Benny is still grinning so widely and Dean can't help it. He presses against Benny's side and when Benny puts his arm around him, he feels safer than he did in a long, long time.

Yeah he wishes this was his life.

He wouldn't stop hunting or anything, but it would be a lot easier with Benny at his side. Not just as a friend, but as his…boyfriend.

Dean sighs unhappily, when Benny takes his arm away and opens the door again for him. Well he does like that, but he wouldn't say it out loud.

Neither of them says anything on the way back to the crappy motel, but Dean is relieved, when he sees that the lights are still out in his room. Maybe Sam is still gone. That means...

Dean groans quietly.

That means nothing. Since Benny isn't his boyfriend. Sure they could still hang out and drink some more beer, but it wouldn't be what Dean wants right now. What he needs.

"So." Benny says, when they are out of the car and right in front of Dean's door. Benny seems a bit unsure now. Gone is the confident man from earlier.

"So." Dean says as well, because apparently he is stupid like that. Benny does grin at that and when he looks up, Dean can see that he is really nervous.

"Good enough for a first date?" Benny asks quietly and Dean tilts his head, in a way Castiel does, when he doesn't understand something.

"What?" Dean says quietly and Benny chuckles.

"I know, I know. I could've tried a bit harder, but I thought it was a good start and next time you can pick out a date for us. If…there is a next time." Benny says and Dean tries to understand his words, because yeah Benny is still talking in English, but the words don't make sense.

Until they do.

That's why Benny was such a gentleman and why he had the urge to touch Dean a lot more today. He…he had asked Dean out earlier. This wasn't just a night between friends. Even Sam had understood that, because he insisted on Dean's nice clothes.

"I would l-like that." Dean says and Benny grins at him.

"I still have to clean up my latest hunt, but maybe Saturday?" Benny asks full of hope and Dean nods. He doesn't care if Sammy has something planned for them. He would do anything for another date with Benny.

"Yeah sounds good." Dean whispers and somehow Benny comes even closer. Dean is pressed with his back against the door and looks up at the vampire.

"Cher." Benny whispers and Dean sees how Benny looks at his lips. Dean is pretty sure he can't form any words right now, so he just nods. He really wants to kiss Benny.

Benny kisses him first.

It's a shy kiss and somehow it fits Benny. Luckily, he puts his hands on Dean's cheeks, because Dean is sure his legs would've given up from this kiss alone and then Benny opens his mouth. Dean groans and Benny chuckles.

Dean can feel it.

He isn't sure how long they are kissing, but Dean feels a bit lightheaded after it. Benny winks at him, when he has his breath under control again.

"Yeah that's…" Benny says and Dean nods. Because yeah. He feels the same. He can't actually say it, but he hopes Benny understands. Seeing his wide smile, he probably does.

"Happy Valentine’s." Benny says then and Dean laughs. Oh god. It's Valentine's Day! That's why Sam was out on a date and that's why the restaurant looked so weird.

"Best Valentine’s ever." Dean says quietly. Well, it would've been only better, if Dean had actually known that this was a date. But sometimes he is an idiot like that.

"So, Saturday?" Dean asks happily and Benny nods.

He carefully presses his lips against Dean's burning cheek.

"Text me and…goodnight, Cher." Benny whispers and with that, he actually turns around and walks back to his car. Dean still leans against the door and watches him go. When Benny drives away, he waves at him.

"Fuck, I'm in love." Dean whispers and then turns around to open the door. Just as he thought, Sam isn't back, so Dean falls face first on his bed and starts laughing.

Oh god. He just had his first date with Benny on Valentine’s Day and didn't even realize it. That would be a fantastic story to tell his kids.

Dean sighs happily and grabs his phone.

_"Miss you already, xx"_

**Author's Note:**

> Find me on [tumblr](https://notfunnydean.tumblr.com)


End file.
